About Gusto
At Gusto, we're on a mission to grow the small business economy. We handle the hard stuff—like payroll, health insurance, 401(k)s, and HR—so owners can focus on their craft and customers. With teams in Denver, San Francisco, and New York, we’re proud to support more than 400,000 small businesses across the country, and we’re building a workplace that represents and celebrates the customers we serve. Learn more about our Total Rewards philosophy.
About the Role:
Gusto's Benefits Sales team is launching a new Business Insurance (BI) vertical, a rapidly growing segment poised to scale quickly. We are looking for a systems-minded, AI-curious Senior Sales Operations Analyst to be the primary Sales Operations thought partner for this new vertical. Your role will involve designing, implementing, and optimizing processes, and creating reports to track performance.
This is your opportunity to help build the foundation of a rapidly growing and impactful area within Gusto’s business as a Senior Sales Operations Analyst supporting the Benefits Sales team. You will analyze data from various systems and develop AI-driven solutions to boost productivity for over 80 sales representatives across two existing segments, while also influencing the future of the new Business Intelligence (BI) team.
About the Team:
The Revenue Operations team supporting the Benefits Sales organization will collaborate closely with sales leadership to empower a fast-paced sales team that drives one of Gusto's key growth areas. The Benefits Sales team consists of two segments: Health Insurance and the newly established Business Insurance team.
Our work scope includes quotas, pipeline health, forecasting, process design, data integrity, and go-to-market strategy, with an increasing emphasis on AI-driven optimization. Our team values curiosity, communication, and a commitment to assist over 80 representatives in operating efficiently and confidently.
Here’s what you’ll do day-to-day:
- Process & Systems Optimization
- Design and implement the BI Sales engine: Lead the creation and deployment of AI-driven workflows that automate manual processes and boost sales productivity.
- Create a scalable system for tracking quotas, assigning territories, and modeling commissions, capable of expanding from 2 representatives to 60 within a year.
- Analytics & Insights
- Build and automate dashboards in Salesforce to monitor lead conversion, analyze funnel performance, sales activity, identify trends, and opportunities for AI use cases.
- Provide clear and actionable recommendations that link data insights to automation or process improvements.
- AI & Workflow Innovation
- Actively identify and prototype AI tools (such as content generation, analytics copilots, and call coaching) to eliminate manual friction in the sales process.
- Examine existing workflows and rep performance to pinpoint bottlenecks and offer actionable recommendations that link data insights to automation and process enhancements.
- Cross-Functional Partnership
- Act as a trusted advisor to the Head of Sales, Enablement, Finance, Analytics, and BizTech to facilitate progress, guide change management, and drive adoption.
- Identify and address risks, uncertainties, and opportunities to enhance how AI and automation drive business outcomes.
- Facilitate go-to-market readiness for new processes, AI workflows, and product updates by creating documentation and operational requirements.
Here’s what we're looking for:
- Experience: 5+ years in Sales Ops, RevOps, or a similar analytical GTM role, ideally in a fast-paced SaaS or Fintech environment.
- Salesforce Expert: High proficiency in Salesforce; you can identify data issues, audit pipelines, and build reports that leaders actually use.
- Proficient in AI and Automation: Skilled at evaluating AI tools and automation solutions to identify opportunities for improving productivity. Experienced in prototyping simple workflows and incorporating AI into operational processes (no engineer-level skills required).
- Builder’s Mindset: You excel in environments where you build the plane while flying it, and you enjoy transforming complex problems into repeatable playbooks.
- Analytical Proficiency: Proficient in creating reports and dashboards using Salesforce, Tableau, Looker, Excel, and Google Sheets.
- Curious & Adaptable: A proactive learner who looks for the best solution to a problem, whether that involves an AI prototype or a simple process change.
- A first-principles problem solver capable of breaking down ambiguous issues, testing hypotheses, and developing structured solutions.
- Excellent Communication: Excellent communication skills with the ability to simplify complex information for stakeholders, providing written and verbal updates that align senior leadership with stakeholders.
Preferred Qualifications
- Experience in payroll, HR tech, or SMB SaaS go-to-market motions.
- Experience designing or implementing automations, AI workflows, or similar tooling.
- Track record of building strong cross-functional relationships across Sales, BizTech, and Analytics.
- Experience building systems to support new sales motions.
- Comfort with fast iteration, experimentation, and testing in live sales environments.
Our cash compensation amount for this role is $104,490 to $128,000 for Denver, Atlanta & Las Vegas. $126,530 to $155,000 for San Francisco & New York. $97,960 to $120,000 for Phoenix. Final offer amounts are determined by multiple factors including candidate location, experience and expertise and may vary from the amounts listed above.
Gusto has physical office spaces in Denver, San Francisco, and New York City. Employees who are based in those locations will be expected to work from the office on designated days approximately 2-3 days per week (or more depending on role). The same office expectations apply to all Symmetry roles, Gusto's subsidiary, whose physical office is in Scottsdale.
Note: The San Francisco office expectations encompass both the San Francisco and San Jose metro areas.
When approved to work from a location other than a Gusto office, a secure, reliable, and consistent internet connection is required. This includes non-office days for hybrid employees.
Our customers come from all walks of life and so do we. We hire great people from a wide variety of backgrounds, not just because it's the right thing to do, but because it makes our company stronger. If you share our values and our enthusiasm for small businesses, you will find a home at Gusto.
Gusto is proud to be an equal opportunity employer. We do not discriminate in hiring or any employment decision based on race, color, religion, national origin, age, sex (including pregnancy, childbirth, or related medical conditions), marital status, ancestry, physical or mental disability, genetic information, veteran status, gender identity or expression, sexual orientation, or other applicable legally protected characteristic. Gusto considers qualified applicants with criminal histories, consistent with applicable federal, state and local law. Gusto is also committed to providing reasonable accommodations for qualified individuals with disabilities and disabled veterans in our job application procedures. We want to see our candidates perform to the best of their ability. If you require a medical or religious accommodation at any time throughout your candidate journey, please fill out this form and a member of our team will get in touch with you.
Gusto takes security and protection of your personal information very seriously. Please review our Fraudulent Activity Disclaimer.
Personal information collected and processed as part of your Gusto application will be subject to Gusto's Applicant Privacy Notice.
Top Skills
Similar Jobs at Gusto
What you need to know about the Chicago Tech Scene
Key Facts About Chicago Tech
- Number of Tech Workers: 245,800; 5.2% of overall workforce (2024 CompTIA survey)
- Major Tech Employers: McDonald’s, John Deere, Boeing, Morningstar
- Key Industries: Artificial intelligence, biotechnology, fintech, software, logistics technology
- Funding Landscape: $2.5 billion in venture capital funding in 2024 (Pitchbook)
- Notable Investors: Pritzker Group Venture Capital, Arch Venture Partners, MATH Venture Partners, Jump Capital, Hyde Park Venture Partners
- Research Centers and Universities: Northwestern University, University of Chicago, University of Illinois Urbana-Champaign, Illinois Institute of Technology, Argonne National Laboratory, Fermi National Accelerator Laboratory
